(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 176896
• Molecular Formular: C27H44O9
• Molecular Mass: 512.63286
• Monoisotopic Mass: 512.29853299
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)([C@@H](O)C)O)C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](O[C@@H]2CC[C@]3([C@@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@H]2CC[C@]3(O)[C@@H](O)C)C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H44O9/c1-13(28)27(34)11-8-18-16-5-4-14-12-15(6-9-25(14,2)17(16)7-10-26(18,27)3)35-24-21(31)19(29)20(30)22(36-24)23(32)33/h13-22,24,28-31,34H,4-12H2,1-3H3,(H,32,33)/t13-,14+,15+,16+,17-,18-,19-,20-,21+,22-,24+,25-,26-,27-/m0/s1
• InChIKey: DUXHVCKABSGLJH-CWTJUICISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (3α,5β,20S)-17,20-Dihydroxypregnan-3-yl β-D-Glucopyranosiduronic Acid; 17,20α-Dihydroxy-5β-pregnan-3α-yl, β-D-Glucopyranosiduronic Acid; Pregnanetriol 3α-O-β-D-Glucuronide

Database IDs

• CAS Number: 74915-85-8
• PubChem SID: 164232806
• PubChem CID: 71751757

CALCULATED PROPERTIES

• Acid pKa: 3.4672441
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -0.61970526
• LogD (pH = 7.4): -1.9814811
• Log P: 1.4034375
• Molar Refractivity: 127.5126 cm^3
• Polarizability: 51.9437 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P705170

Pregnanetriol 3α-O-β-D-Glucuronide is the glucuronide conjugate of Pregnanetriol (P705160). Urinary Pregnanetriol 3α-O-β-D-Glucuronide can be used for both the immediate prediction and the detection of ovulation. Measurement of urinary Pregnanetriol 3α-O

REFERENCES

• Saisho, S. et al.: Screening, 4, 193 (1996)
• Bedolla-Tovar, N. et al.: J. Steroid Biochem., 24, 921 (1996)